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Bromination and Debromination of Cholesterol Experiment

Learn the nucleophilic attack by alkene on bromine to purify cholesterol in a lab setting. Follow procedures and safety tips for successful outcomes.

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Bromination and Debromination of Cholesterol Experiment

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  1. Chapter 20Bromination/Debromination of Cholesterol

  2. Purpose • This reaction involves nucleophilic attack by the alkene on bromine, forming a tertiary carbocation with bromonium ion character. This ion is attacked from the backside by bromide ion to form dibromocholesterol in the trans and diaxial configuration. • This reaction is employed in the practical purpose of purifying cholesterol.

  3. Comments • Follow p. 360, 362(microscale). • Follow the lab handout for all experimental procedures. Wearing rubber gloves is necessary during this lab. You will work with toxic and corrosive compounds. • Calculate yield. Moderate to good yields should be achieved. (Moles Product / Moles Starting Material) x 100 = % Yield • Answer question 2, p. 364.

  4. Safety • Avoid getting the acetic acid and bromine solution on skin. • Be gentle when stirring in a test tube as it is easy to punch a stirring rod through the bottom of the test tube. • Filtrate (liquid waste) contains halogenated material and must be placed into the halogenated waste container.

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